Sulfuric Acid → 3-(Tert-butoxy)-1-iodohexane

HRID 1439666노트

반응식

HRID 1439666 반응식
ClCCC(O)CCC.[I-].[Na+].[I:11][CH2:12][CH2:13][CH:14]([OH:18])[CH2:15][CH2:16][CH3:17].S(=O)(=O)(O)O.[CH3:24][C:25](=[CH2:27])[CH3:26]>C(Cl)Cl.CC(=O)CC>[C:25]([O:18][CH:14]([CH2:15][CH2:16][CH3:17])[CH2:13][CH2:12][I:11])([CH3:27])([CH3:26])[CH3:24]

참가 물질

8

반응물 5

HCID 1118Sulfuric AcidHCID 5238Sodium IodideHCID 8255IsobutyleneHCID 189210041-Iodohexan-3-OLHCID 189210071-Chlorohexan-3-ol

생성물 1

HCID 204656183-(Tert-butoxy)-1-iodohexane

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6569Methyl Ethyl Ketone용매

실험 절차

A mixture of 23.4 g. of 1-chloro-3-hexanol [Fourneau, et. al., Bull. Soc. Chem. France, 25, 367 (1919)] in 300 ml. of 2-butanone containing 30 g. of sodium iodide is stirred at the reflux temperature for 18 hours. The cooled solution is filtered and the mother liquor is taken to dryness. Distillation of the residue affords 32.9 g. (84%) of 1-iodo-3-hexanol, b.p. 105° C. (10 mm). Treatment of this material in 500 ml. of methylene chloride, containing 4 ml. of concentrated sulfuric acid, with isobutylene according to the procedure described in Example 492 gives 27 g. of crude material. Chromatography on florisil affords 16 g. of product; λmax. 7.22 and 7.37 μ (tert-butyl group).

후처리

  1. additionA mixture of 23.4 g
  2. filtrationThe cooled solution is filtered
  3. distillationDistillation of the residue
  4. customaffords 32.9 g
  5. customgives 27 g
  6. customChromatography on florisil affords 16 g

출처 및 근거

ORD 기록
ord-b510ca0b84a741ebbe48187a420be926
출처 데이터셋
uspto-grants-1977_11
특허 번호
US04060540

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